This invention relates to flavors and specifically to modified pineapple ketone.
The prior art does not show the alkoxy alkyl ether dihydrofuranone compound of the invention. Nor is there a suggestion in the prior art of the substantial oxidative stability increases beneficially provided by the alkoxy alkyl ether dihydrofuranone compounds of the invention over the dihydrofurans and dihydrofuranones of the prior art.
Pineapple ketone is the common name for the chemical 2,5-dimethyl-4-hydroxy-3(2H)-furanone. This is a compound found in pineapples, strawberries, raspberries, meats, and other foods. It has been found in cooked, roasted and fermented foods including coffee, roasted filbert, roasted almond and soy sauce. Pineapple ketone is known to be formed by the non-enzymatic browning process that occurs during roasting and baking.
Because of its cotton-candy, caramelized-sugar flavor, pineapple ketone is used extensively to compound synthetic flavors. Pineapple ketone reacts readily with amines, aldehydes and oxygen. In such cases, the pineapple ketone content of the flavors is reduced, lowering the effectiveness of the flavor.
When pineapple ketone is used in chewing-gum, it is quickly "washed out" by the chewing process, resulting in rapid loss of flavor. This "washing out" effect is due to pineapple ketone being water soluble.
Willhalm et al., U.S. Pat. No. 3,455,702; Herman et al, U.S. Pat. No. 3,697,291; and Demole, U.S. Pat. No. 3,983,885 disclose that flavor may be imparted to foodstuffs, beverages, meat, or tobacco by incorporating therein a minor proportion of a dihydrofuran, such as, methyl and ethyl ethers.
Britten-Kelly, et al., U.S. Pat. No. 4,383,943, disclose that the 1'-ethoxyethyl ether of isoeugenol "retains the same odor characteristics as isoeugenol", unlike other cited derivatives. One of the advantages cited for the subject ether is that it is stable to discoloration in fragranced soaps after six months of storage, unlike isoeugenol which causes discoloration.
S. Arctander, "Perfume and Flavor Chemicals", published by the author, Montclair (1969), describes the use of numerous 1'-alkoxyalkyl ethers as useful for flavor and fragrance compositions. Several examples are shown below: ##STR2##